WO2003035628A1 - Procede de preparation d'alcoxycarbonylamino-triazines - Google Patents

Procede de preparation d'alcoxycarbonylamino-triazines Download PDF

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Publication number
WO2003035628A1
WO2003035628A1 PCT/EP2002/011837 EP0211837W WO03035628A1 WO 2003035628 A1 WO2003035628 A1 WO 2003035628A1 EP 0211837 W EP0211837 W EP 0211837W WO 03035628 A1 WO03035628 A1 WO 03035628A1
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WIPO (PCT)
Prior art keywords
triazine
reaction
formula
mol
alkanol
Prior art date
Application number
PCT/EP2002/011837
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German (de)
English (en)
Inventor
Jörg Schneider
Günter Scherr
Hans Schupp
Andreas Eichfelder
Alain Robert
Martin Reif
Original Assignee
Basf Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE2001151564 external-priority patent/DE10151564A1/de
Priority claimed from DE2002118617 external-priority patent/DE10218617A1/de
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to BRPI0213227-3A priority Critical patent/BR0213227B1/pt
Priority to AT02782982T priority patent/ATE483695T1/de
Priority to DE50214702T priority patent/DE50214702D1/de
Priority to US10/491,194 priority patent/US7169923B2/en
Priority to EP02782982A priority patent/EP1440065B1/fr
Priority to JP2003538144A priority patent/JP4571801B2/ja
Publication of WO2003035628A1 publication Critical patent/WO2003035628A1/fr
Priority to US11/609,674 priority patent/US7371856B2/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • C07D251/70—Other substituted melamines

Definitions

  • the present invention relates to a new process for the preparation of alkoxycarbonylamino-triazines by reacting di- or tria-inotriazines with dimethyl carbonate in the presence of an alkanol and an alkali metal or alkaline earth metal methoxide as a base.
  • EP-A-624 577 discloses the preparation of alkoxycarbonylamino-triazines by reacting triazines, for example melamine, with carbonic acid esters in the presence of a base.
  • triazines for example melamine
  • melamine with a carbonic acid ester e.g. Dimethyl carbonate
  • an alkali alkanolate based on the alkanol on which the carbonic acid ester is based, here e.g. Methanol
  • melamine e.g. with dimethyl carbonate in the presence of a higher alcohol, e.g. butanol or 2-ethylhexanol
  • the corresponding sodium alkanolate here e.g. Sodium butanolate or sodium (2-ethylhexanolate
  • the working up of the alkoxycarbonylamino-triazines described in EP-A-624 577 from the reaction mixtures obtained is not particularly advantageous.
  • the reaction mixtures are acidified or converted into an acidic solution. This is followed by extraction with an organic solvent. The organic extracts are then dried and the solvent is removed. Alternatively, after acidifying a solid isolated by filtration, which is then washed and dried.
  • Another object of the present invention was to provide a new workup method for reaction mixtures which are obtained in the preparation of alkoxycarbonylamino-triazines.
  • a cost-intensive filtration technique should be avoided and the number of chemical components in the process should not be increased any further.
  • Y 1 is hydrogen, -CC 4 -alkyl, optionally substituted by -CC 4 -alkyl, -C-C 4 -alkoxy or halogen-substituted phenyl or a radical of the formula NR 5 R 6 and
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently of one another are hydrogen or a radical of the formula COOX or X, where X is C 3 -C 3 -alkyl, the carbon structure of which is 1 or 2 acidic Atoms in ether function can be interrupted, stands, mean
  • radicals R 1 to R 4 or if Y 1 is NR 5 R 6 , at least one of the radicals R 1 to R 6 is the radical COOX,
  • Y 2 is hydrogen, -CC 4 -alkyl, amino or phenyl optionally substituted by Ci-Ci-alkyl, -C ⁇ C 4 -alkoxy or halogen, with the proviso that in formula II if Y 2 is not A ino , at least one of the radicals R 1 to R 4 is hydrogen, and
  • R 1 to R 4 each have the meaning given above,
  • Residues Y 1 , Y 2 and X are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
  • Residues X are furthermore, for example, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isoctyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, isotridecyl , 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3-propoxypropyl, 2- or 4-methoxybutyl, 2nd - or 4-ethoxybutyl, 3, 6-dioxaheptyl, 3, 6-dioxaoctyl, 3, 7-dioxaoc
  • Residues Y 1 and Y 2 are also, for example, phenyl, 2-, 3- or 4-methylphenyl, 2-, 3- or 4-ethylphenyl, 2, 4-dimethylphenyl, 2-, 3- or 4-methoxyphenyl , 2-, 3-, or 4-ethoxyphenyl, 2, 4-dimethoxyphenyl, 2-, 3- or 4-fluorophenyl or 2-, 3- or 4-chlorophenyl.
  • Suitable C 1 -C 3 alkanols which can be used in the process according to the invention are, for example, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol, tert-butanol, pentanol, isopentanol, neopentanol, tert-pentanol, hexanol, 2 -Methylpentanol, heptanol, octanol, 2-ethylhexanol, isooctanol, nonanol, isononanol, decanol, isodecanol, undecanol, dodecanol, tridecanol, isotridecanol, 2-methoxyethanol, 2-ethoxyethanol, 2-propoxyethanol, 2-butoxyethanol, 2- or 3- Methoxypropanol, 2- or 3-ethoxypropanol, 2- or
  • C 1 -C 3 alkanols is preferred, the use of CC 7 alkanols being particularly mentioned.
  • the alcohols used in the process according to the invention can be used either individually or as mixtures with one another. In the latter case, the number of mixing partners and the mixing ratios can be arbitrary.
  • Suitable alkali or alkaline earth metal methanolates which can be used according to the invention are e.g. Lithium, sodium, potassium, magnesium or calcium methoxide.
  • Alkali or alkaline earth metal methanolate can be used either in the solid state or in dissolved or suspended form.
  • preferred solvents / diluents are, in particular, the alcohols specified above, alone or as a mixture with one another.
  • other inert diluents known per se and customary can also be used.
  • the proportion by weight of methanol, based on the total weight of all alcohols used in the process (including methanol) is less than or equal to 20% by weight, preferably less than 15% by weight.
  • phase transfer catalysts of the type as described in Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A 19, pages 239 to 248, for example, be used.
  • Further catalysts can be metal salts or complexes, preferably oxides, chalcogenates, carbonates or halides of the alkali, alkaline earth or transition metals.
  • metal salts or complexes preferably oxides, chalcogenates, carbonates or halides of the alkali, alkaline earth or transition metals. Examples include lithium chloride, magnesium chloride or sodium carbonate.
  • 1 to 50 mol, preferably 3 to 30 mol, of alkanol are generally used per molar equivalent of substitutable amino groups in the triazine of the formula II.
  • Substitutable amino groups in the sense of the invention are understood to mean the following groupings: —H or —NH—.
  • 0.1 to 10 mol, preferably 1 to 3 mol, of dimethyl carbonate are generally used in the process according to the invention per mol equivalent of substitutable amino groups in the triazine of the formula II.
  • alkali metal or alkaline earth metal methoxide are generally used in the process according to the invention per mol equivalent of substitutable amino groups in the triazine of the formula II.
  • crystallizer are in general 10 ⁇ 10 to 10 wt .-%, preferably 10 -3 to 1 wt .-% catalyst, based on the weight of the triazine of the formula II, to use.
  • the process according to the invention is generally carried out at a temperature of 20 to 180 ° C., preferably 50 to 100 ° C. It is usually carried out under atmospheric pressure, but the use of elevated pressure, as a rule up to 8 bar, is possible.
  • R 1 to R 6 each have the abovementioned meaning, with the proviso that three of these radicals each represent hydrogen and the remaining three of these radicals each represent a radical of the formula COOX, in which X has the abovementioned meaning, by means of the process according to the invention.
  • formula I also includes those products which i) have only a single COOX radical in the molecule in which X is methyl and / or ii) have a plurality of COOX radicals in the molecule in which X is exclusively methyl, such products are alone not to be understood as target products of the method according to the invention. At most, they are obtained in a mixture with other products which a) have only one COOX radical in the molecule, in which X is different from methyl, and / or b) have more COOX radicals in the molecule, in which at least one X is different of methyl.
  • the process according to the invention is advantageously carried out by introducing triazine II and alkanol and then metering in alkali metal or alkaline earth metal methoxide, in the solid state and / or dissolved in alkanol, and dimethyl carbonate in any order, the dosing of alkali metal or alkaline earth metal methoxide and dimethyl carbonate being complete before the start of the reaction or partly before the start of the reaction and partly after the start of the reaction.
  • the desired alkanol ratios can be set, as a result of which the product spectrum can be influenced in a targeted manner.
  • alkoxycarbonylaminotriazines according to the invention can be prepared in various variants (A-F).
  • triazine II, alkanol and dimethyl carbonate are introduced and part of the alkali metal or alkaline earth metal methoxide, which is partly in the dissolved and partly in the solid state, is metered in before the start of the reaction and the rest after the start of the reaction.
  • triazine II, alkanol and dimethyl carbonate are introduced and part of the alkali metal or alkaline earth metal methoxide, which is either in dissolved form or in the solid state, is metered in before the start of the reaction and the rest after the start of the reaction.
  • catalysts are added before or after the start of the reaction.
  • different alkali methanolates are added before or after the start of the reaction (e.g. lithium methoxide and sodium methoxide).
  • the reaction can also be carried out in such a way that melamine is metered in stepwise or continuously during the reaction.
  • the process according to the invention can be carried out in conventional reaction apparatus, for example a boiler or tubular reactor. If the new process is carried out in such a way that the molar ratio of triazine of the formula II: alkanol is as high as possible, the use of apparatuses with a mixing action in the case of highly viscous or inhomogeneous reaction mixtures, for example kneading reactors, is preferred. It is also possible to use self-cleaning devices with a mixing effect. Such apparatuses are known per se and are commercially available. Suitable reactors of this type are, for example, the chamber reactor, the circulation reactor or the screw reactor. The resulting reaction mixture is advantageously worked up in the absence of additional solvents.
  • the alkanolic reaction mixture is brought into direct contact with acid, 5 either by metering in acid or by converting the reaction mixture into a suitable acid.
  • the acid can be added in a concentrated manner and water can be added during or after the acid has been metered in. Especially when using aqueous or highly concentrated
  • a suitable mixture must be guaranteed for 10 acids during dosing.
  • all customary and industrially available organic and inorganic acids optionally also in a mixture with one another, in any concentration, but preferably as 30 to
  • aqueous solutions 15 85% by weight aqueous solutions can be used.
  • an aqueous and an alkanolic phase form, which are separated from one another.
  • the separation of the phases is temperature and pH dependent, so that the addition of additional water at a
  • the target products result directly as a 10 to 80% by weight alkanol solution. Subsequent concentration of the 30 alkanolic phase simultaneously removes some of the water carried along (e.g. with butanol), so that further drying steps, e.g. the addition of drying agents are not necessary.
  • reaction mixture can be worked up after neutralization with any acid, of course also by extraction, washing and / or by filtration.
  • the new process which can be carried out both continuously and discontinuously, delivers the target products in high yield and purity.
  • alkoxycarbonylamino-triazines obtainable by means of the process according to the invention are valuable coating materials.
  • the following examples are intended to explain the invention in more detail.
  • the main components of the mixture could be identified as 2,4,6-tris (heptyloxycarbonylamino) -1,3, 5-triazine, 2-methoxycarbonylamino-4, 6-bis (heptyloxycarbonylamino) -1, 3, 5-triazine and 2,4-bis (meth- oxycarbonylamino) -6-heptyloxycarbonylamino-1,3,5-triazine (HPLC, HPLC-MS).
  • Example 3 was carried out analogously to Example 1, but 774 ml of ethanol were used instead of butanol.
  • the main components of the mixture could be identified as 2, 4, 6-tris (ethoxycarbonylamino) -1, 3, 5-triazine, 2-methoxycarbonylamino-4, 6-bis (ethoxycarbonylamino) -1 , 3, 5-triazine and 2,4-bis (methoxycarbonylamino) -6-ethoxycarbonylamino-1,3,5-triazine (HPLC, HPLC-MS).
  • Example 4 was carried out analogously to Example 1, but 1002 ml of 2-propanol were used instead of butanol.
  • the main components of the mixture could be identified as 2, 4, 6-tris (2-propoxycarbonylamino) -l, 3, 5-triazine, 2-methoxycarbonylamino-4, 6-bis (2-propoxy- carbonylamino) -1, 3,5-triazine and 2,4-bis (methoxycarbonylammo) - 6- (2-propoxy) carbonylamino-1,3,5-triazine (HPLC, HPLC-MS).
  • Example 5 was carried out analogously to Example 1, but 385 g of lithium methoxide (10% by weight in methanol) were used instead of sodium methoxide.
  • the main components of the mixture could be identified as 2, 4, 6-trisbutoxycarbonylamino) -1, 3, 5-triazine, 2-methoxycarbonylamino-4, 6-bis (butoxycarbonylammo) -1, 3, 5-triazine and 2,4-bis (methoxycarbonylammo) -6-butoxycarbonylamino-1,3,5-triazine (HPLC, HPLC-MS).
  • Example 7 The reaction mixture was worked up as explained in Example 1 and contained predominantly 2,4,6-tris (butoxycarbonylammo) -1,3,5-triazine, 2-methoxycarbonylamino-4,6-bis (butoxycarbonylamino) -1, 3,5-triazine and 2,4-bis (methoxycarbonylmino) -6-butoxycarbonylamino-1,3,5-triazine (HPLC).
  • Example 7 Example 7
  • Example 7 was carried out analogously to Example 6 but at a pressure of approx. 2 bar and a reaction temperature of 80 ° C.
  • the reaction mixture was worked up as explained in Example 1 and contained predominantly 2,4,6-tris (butoxycarbonylammo) -1,3,5-triazine, 2-methoxycarbonylamino-4,6-bis (butoxycarbonylammo) -1,3, 5-triazine and 2,4-bis (methoxycarbonylammo) -6-butoxycarbonylamino-1,3,5-triazine contained (HPLC).
  • the main components of the mixture could be identified as 2,4,6-tris (methoxycarbonylammo) -1,3,5-triazine, 2-butoxycarbonylamino-4,6-bis (methoxycarbonylammo) -1,3 , 5-triazine and 2, 4-bis (butoxycarbonylamino) -6-methoxycarbonylamino-l, 3, 5-triazine, 2, 4, 6-tris (butoxycarbonylammo) -1, 3, 5-triazine, (HPLC, HPLC-MS).
  • the reaction was carried out analogously to Example 9, but 97 g (1 mol) of aqueous phosphoric acid were used instead of nitric acid after cooling the mixture to about 30 ° C. with stirring (85 wt .-%) and 600 ml of water added. The aqueous phase was separated off and the organic homogeneous phase was washed a further 2 times with 300 ml of water each time.
  • butanolic product solution which predominantly contains 2,4,6-tris (butoxycarbonylammo) -1, 3,5-triazine, 2-methoxycarbonylamino-4,6-bis (butoxycarbonylammo) Contained -1,3,5-triazine and 2,4-bis (methoxycarbonylammo) -6-butoxycarbonylamino-1,3,5-triazine (HPLC, X H, 13 C NMR).
  • Example 13 The reaction was carried out analogously to Example 13, but the melamine was metered in 4 equal portions over the course of 1.5 hours to the dimethyl carbonate, sodium methoxide and butanol. Working up was also carried out as described in Example 13. The result was a 50% by weight butanol solution, the main components being 2,4,6-tris (butoxycarbonylamino) -1,3,5-triazine, 2-methoxycarbonylamino-6-bis (butoxycarbonylamino) -1,3 5-triazine and 2,4-bis (methoxycarbonylammo) -6-butoxycarbonylamino-1,3,5-triazine contained (HPLC, ⁇ -H, 13 C-NMR).
  • 50% by weight solution predominantly contained 2,4,6-tris (butoxycarbonylamino) -1,3,5-triazine (19.5 A%), 2-methoxycarbonylamino-4,6-bis (butoxycarbonylammo) - !, 3, 5-triazine (41.5 A .-%), 2, 4-bis (butoxycarbonylammo) -6-amino-l, 3, 5-triazine (2.8 A .-%), 2 , 4-bis (methoxycarbonylammo) -6-butoxycarbonylamino-l, 3,5-triazine (25.6 A .-%), 2-meth-oxycarbonylamino-4-butoxycarbonylamino-6-amino-l, 3,5-triazine (3.4 A .-%) and Tris (methoxycarbonylammo) -1, 3, 5-triazine (4.6 A .-%).
  • Example 15 The reaction was carried out analogously to Example 15, but the mixture was heated to 80 ° C. within one hour. Subsequently, about 15 l of solvent were distilled off under reduced pressure within 30 minutes. The reaction mixture was stirred at 80 ° C. for a further 2.5 hours and then cooled to 35 ° C. Working up is carried out as described in Example 15. The resulting approx. 50% by weight solution contained predominantly 2,4,6-tris (butoxycarbonylammo) -1, 3,5-triazine (25.9 A .-%), 2-methoxy- carbonylamino-4,6-bis (butoxycarbonylammo) -1,3,5-triazine (44.6 A.
  • 50% by weight solution contained predominantly 2,4,6-tris (butoxycarbonylamino) -1,3,5-triazine (28.1 A.%), 2-methoxycarbonylamino-4,6-bis (butoxycarbonylammo ) - 1, 3, 5-triazine (42.75 A .-%), 2, 4-bis (butoxycarbonylammo) -6-amino-1, 3, 5-triazine (3.0 A .-%), 2, 4-bis (methoxycarbonylammo) -6-butoxycarbonylamino-1, 3, 5-triazine (18.4 A. -%), 2-methoxycarbonylamino-4-butoxycarbonylamino-6-amino-l, 3,5-triazine (4.8 A. -%) and tris (methoxycarbonylammo) -1,3,5-triazine (1.8 A .-%).
  • Example 20 The reaction was carried out analogously to Example 18, but a solvent stream was continuously removed at 85 ° C. during the reaction (distillation). The reaction mixture was worked up as described in Example 15. The 50% by weight product solution contained predominantly tris (butoxycarbonylammo) - 1,3,5-triazine, the content of which was 69 A% (HPLC).
  • Example 20 The 50% by weight product solution contained predominantly tris (butoxycarbonylammo) - 1,3,5-triazine, the content of which was 69 A% (HPLC).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé de préparation d'alcoxycarbonylamino-triazines de formule (I), par réaction de diaminotriazines ou de triaminotriazines avec du diméthylcarbonate en présence d'un alcool et d'un méthanolate alcalin ou alcalinoterreux utilisé comme base.
PCT/EP2002/011837 2001-10-23 2002-10-23 Procede de preparation d'alcoxycarbonylamino-triazines WO2003035628A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
BRPI0213227-3A BR0213227B1 (pt) 2001-10-23 2002-10-23 processo para preparaÇço de alcàxicarbonilaminotriazinas.
AT02782982T ATE483695T1 (de) 2001-10-23 2002-10-23 Verfahren zur herstellung von alkoxycarbonylamino-triazinen
DE50214702T DE50214702D1 (de) 2001-10-23 2002-10-23 Verfahren zur herstellung von alkoxycarbonylamino-triazinen
US10/491,194 US7169923B2 (en) 2001-10-23 2002-10-23 Method for preparing alkoxycarbonylamino-triazines
EP02782982A EP1440065B1 (fr) 2001-10-23 2002-10-23 Procede de preparation d'alcoxycarbonylamino-triazines
JP2003538144A JP4571801B2 (ja) 2001-10-23 2002-10-23 アルコキシカルボニルアミノ−トリアジンの製造法
US11/609,674 US7371856B2 (en) 2001-10-23 2006-12-12 Preparation of alkoxycarbonylaminotriazines

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE10151564.2 2001-10-23
DE2001151564 DE10151564A1 (de) 2001-10-23 2001-10-23 Verfahren zur Herstellung von Alkoxycarbonylamino-triazinen
DE2002118617 DE10218617A1 (de) 2002-04-25 2002-04-25 Verfahren zur Herstellung von Alkoxycarbonylamino-triazinen
DE10218617.0 2002-05-04

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US10491194 A-371-Of-International 2002-10-23
US11/609,674 Division US7371856B2 (en) 2001-10-23 2006-12-12 Preparation of alkoxycarbonylaminotriazines

Publications (1)

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WO2003035628A1 true WO2003035628A1 (fr) 2003-05-01

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Country Status (8)

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US (2) US7169923B2 (fr)
EP (1) EP1440065B1 (fr)
JP (1) JP4571801B2 (fr)
CN (1) CN1268617C (fr)
AT (1) ATE483695T1 (fr)
BR (1) BR0213227B1 (fr)
DE (1) DE50214702D1 (fr)
WO (1) WO2003035628A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006131486A1 (fr) * 2005-06-06 2006-12-14 Basf Aktiengesellschaft Procede de preparation d'un melange reactionnel contenant de l'alcoxycarbonylaminotriazine
WO2006131474A1 (fr) * 2005-06-06 2006-12-14 Basf Aktiengesellschaft Procede de production d'alcoxycarbonylaminotriazine sous forme pulverulente
WO2006131456A1 (fr) * 2005-06-06 2006-12-14 Basf Aktiengesellschaft Procede de recuperation de matieres de valeur a partir de flux produits lors de la concentration de melanges reactionnels a teneur en aminotriazine d'alcoxycarbonyle
WO2006131498A1 (fr) * 2005-06-06 2006-12-14 Basf Aktiengesellschaft Procede de production d'un melange reactionnel renfermant une alcoxycarbonylaminotriazine
US20070196668A1 (en) * 2004-04-14 2007-08-23 Basf Aktiengesellschaft Method For Producing 1,3,5-Triazine Carbamates And Ureas
JP2007532597A (ja) * 2004-04-14 2007-11-15 ビーエーエスエフ　アクチェンゲゼルシャフト カルバマート官能基を有するトリアジン誘導体
US8569423B2 (en) 2007-05-31 2013-10-29 Borealis Agrolinz Melamine Gmbh Triazine derivatives and a method for their production
EP2995613A1 (fr) * 2014-09-09 2016-03-16 Allnex IP S.à.r.l. Procédure de Synthèse pour des carbamates de triazines
EP4282859A1 (fr) * 2022-05-25 2023-11-29 Allnex USA Inc. Agent de reticulation de type triazine carbamate

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10259672A1 (de) * 2002-12-18 2004-07-01 Basf Ag Verfahren zur Herstellung von Alkoxycarbonylamino-triazinen
DE102004018546A1 (de) * 2004-04-14 2005-11-03 Basf Ag Strahlungshärtbare 1,3,5-Triazincarbamate und -harnstoffe
DE102005025900A1 (de) * 2005-06-06 2006-12-07 Basf Ag Verfahren zur Entfernung von Salzen aus einem Alkoxycarbonylaminotriazin enthaltenden Reaktionsgemisch
WO2008156151A1 (fr) * 2007-06-19 2008-12-24 Kobelco Eco-Solutions Co., Ltd. Procédé de simulation, appareil de simulation, procédé de traitement biologique et appareil de traitement biologique
JP5677851B2 (ja) * 2007-12-31 2015-02-25 ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツングＢＡＳＦ Ｃｏａｔｉｎｇｓ ＧｍｂＨ 硬化性アルコキシカルボニルアミノ組成物、被覆、および方法
DE102008061139A1 (de) * 2008-12-09 2010-06-10 Borealis Agrolinz Melamine Gmbh Verfahren zur Herstellung von Triazincarbamaten unter Verwendung von Chlorformiaten
JP6461016B2 (ja) * 2013-03-05 2019-01-30 オルネクス ネザーランズ ビー．ヴイ． トリアジンカルバマートの製造方法
TWI805415B (zh) * 2022-06-23 2023-06-11 長春人造樹脂廠股份有限公司 三(烷氧基羰基氨基)三嗪組合物、包含其之塗料組合物及其製法

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JP4691094B2 (ja) * 2004-04-14 2011-06-01 ビーエーエスエフ ソシエタス・ヨーロピア カルバマート官能基を有するトリアジン誘導体
US20070196668A1 (en) * 2004-04-14 2007-08-23 Basf Aktiengesellschaft Method For Producing 1,3,5-Triazine Carbamates And Ureas
JP2007532598A (ja) * 2004-04-14 2007-11-15 ビーエーエスエフ　アクチェンゲゼルシャフト １，３，５−トリアジンカルバメート及び−尿素の製造方法
JP2007532597A (ja) * 2004-04-14 2007-11-15 ビーエーエスエフ　アクチェンゲゼルシャフト カルバマート官能基を有するトリアジン誘導体
US8471007B2 (en) * 2004-04-14 2013-06-25 Basf Se Method for producing 1,3,5-triazine carbamates and ureas
JP4814218B2 (ja) * 2004-04-14 2011-11-16 ビーエーエスエフ ソシエタス・ヨーロピア １，３，５−トリアジンカルバメート及び−尿素の製造方法
WO2006131474A1 (fr) * 2005-06-06 2006-12-14 Basf Aktiengesellschaft Procede de production d'alcoxycarbonylaminotriazine sous forme pulverulente
WO2006131486A1 (fr) * 2005-06-06 2006-12-14 Basf Aktiengesellschaft Procede de preparation d'un melange reactionnel contenant de l'alcoxycarbonylaminotriazine
WO2006131498A1 (fr) * 2005-06-06 2006-12-14 Basf Aktiengesellschaft Procede de production d'un melange reactionnel renfermant une alcoxycarbonylaminotriazine
JP2008542426A (ja) * 2005-06-06 2008-11-27 ビーエーエスエフ ソシエタス・ヨーロピア 粉末状アルコキシカルボニルアミノトリアジンの製造方法
WO2006131456A1 (fr) * 2005-06-06 2006-12-14 Basf Aktiengesellschaft Procede de recuperation de matieres de valeur a partir de flux produits lors de la concentration de melanges reactionnels a teneur en aminotriazine d'alcoxycarbonyle
US8030485B2 (en) 2005-06-06 2011-10-04 Basf Aktiengesellschaft Process for the preparation of pulverulent alkoxycarbonylaminotriazine
US8569423B2 (en) 2007-05-31 2013-10-29 Borealis Agrolinz Melamine Gmbh Triazine derivatives and a method for their production
EP2995613A1 (fr) * 2014-09-09 2016-03-16 Allnex IP S.à.r.l. Procédure de Synthèse pour des carbamates de triazines
WO2016037973A1 (fr) * 2014-09-09 2016-03-17 Allnex Ip S.À.R.L. Procédé de préparation de carbamates de triazine
KR20170054392A (ko) * 2014-09-09 2017-05-17 올넥스 아이피 에스에이알엘 트리아진 카르바메이트의 제조 방법
US10071972B2 (en) 2014-09-09 2018-09-11 Allnex Netherlands B.V. Process for the preparation of triazine carbamates
KR102446766B1 (ko) 2014-09-09 2022-09-22 알넥스 네덜란드 비. 브이. 트리아진 카르바메이트의 제조 방법
EP4282859A1 (fr) * 2022-05-25 2023-11-29 Allnex USA Inc. Agent de reticulation de type triazine carbamate

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EP1440065B1 (fr) 2010-10-06
JP2005511546A (ja) 2005-04-28
CN1575285A (zh) 2005-02-02
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DE50214702D1 (de) 2010-11-18
BR0213227B1 (pt) 2012-12-25
US7371856B2 (en) 2008-05-13
US7169923B2 (en) 2007-01-30
JP4571801B2 (ja) 2010-10-27
EP1440065A1 (fr) 2004-07-28
ATE483695T1 (de) 2010-10-15
US20070083047A1 (en) 2007-04-12
US20040249149A1 (en) 2004-12-09

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